Methyl iodide → N-(4-chlorobenzyl)-6-(hydroxymethyl)-8-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Participants

Reaction Steps

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-8-iodo-3-quinolinecarboxamide(6.5 g) in anhydrous DMF (116.7 mL) is heated to 65° C. to solubilize the starting material. The solution is allowed to cool to room temperature. To this solution is added K2CO3 (7.68 g) and CH3I (8.65 mL). The reaction is stirred at room temperature overnight. The reaction is poured into H20 (1L) to precipitate the product. The solid is filtered, adsorbed onto silica, and chromatographed in 2 batches (eluent 100% CH2Cl2 (3L), 0.5% MeOH in CH2Cl2 (1L), and 1% MeOH in CH2Cl2 (9L)). Product-containing fractions are combined and condensed to afford 3.6 g (54%) of the desired product as a white solid.

Provenance & Evidence